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October’s Very Own: Recapping Some of Drake’s Best Moments in 2023

The Toronto rapper’s year consisted of headphones, controversy, and triumph.

Drake’s 2023 was one for the books as it was not only one of his most successful musically but also had him generating an immense amount of headlines (no pun intended). From his highly successful It’s All A Blur tour to dropping his eighth solo studio album For All The Dogs, which set records in its own right, the Toronto rapper had the internet on smash.

Some of Drizzy’s actions weren’t without criticism and controversy. Perhaps his imperfect nature makes fans and critics unable to keep his name out of their mouths or fingers. Below, we’ve compiled some of Drake’s biggest and best moments of the year to honor his birth month.

  • Bringing Out Dipset In Harlem

    Drake has a history of digging into music’s past and celebrating it. In January, the Canadian rapper did so again during his debut performance at Harlem’s legendary Apollo Theater. Capping off the show, the Toronto rapper brought out neighborhood natives The Diplomats for a performance of “I Really Mean It,” “Dipset Anthem,” and “We Fly High (Ballin).” “These guys from Harlem made us dress different, talk different, walk different, rap different in Canada,” he said while draped in Cam’ron’s iconic pink mink coat. During his own set, Drizzy performed songs from different eras of his over decade-long career, including "Marvin's Room," "Best I Ever Had," "Hold On, We're Going Home," "One Dance," and "God's Plan," among others.

  • Media Appearances

    Drake is notorious for not doing many interviews throughout his career, so it was a surprise when he did a few (albeit not by journalists). From his sit down with Lil Yachty for Moody Conversations back in February to his more recent and infamous back-and-forth with podcaster Bobbi Althoff in August (which has now been deleted), the Toronto rapper provided a little insight into his life as of late. Drizzy also did a few New York-based media appearances by stopping by On The Radar for a freestyle (along with Central Cee) and even a Sidetalk cameo in July.

  • Honored with Key to Memphis

    In June, Drake was recognized by local officials from Memphis and Shelby County during a visit to the city – one in which he has ties by way of family. The Toronto rapper was honored with a key to the city by Mickell Lowery, chairman of the Shelby County Commission, prior to him sharing some kind remarks about the rap veteran. “In Memphis you know, we love our own. Drake, we always say Memphis music touches the world, and like I told you, you’ve got a lot of Memphis blood in you, and you’re definitely touching the world,” Lowery told Drizzy. “We appreciate the music, we appreciate you putting Memphis all in your music, on the map.”

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  • Collecting Bras On Tour

    Toward the start of Drake’s It’s All A Blur tour, he made a lot of headlines after his female fans caught his attention by throwing their bras at him either while he was on stage or during the walk up to it. During his stop at the Barclays Center in Brooklyn, a fan tossed her size 36G bra at the Toronto rapper, which caused him to pause and call for her identity (which was later revealed). In August, he rocked a custom 46J Bra as a durag after a fan tossed it on stage during his show in Seattle. Then, in September, Drizzy revealed all the bras he acquired on the road, taking a selfie with the undergarments.

  • Poetry Book Release

    Drake is a man of creativity; not all of it can be presented in musical form. In June, the 6 God released his debut book of poetry, Titles Ruin Everything: A Stream of Consciousness. A collaboration with frequent co-writer and contributor Kenza Samir, the work accompanies Drizzy’s newest album, For All The Dogs. According to poet and MacArthur Fellow recipient Hanif Abdurraqib, the book is one “of puns” and “silly lil’ jokes” but one that is not seriously attempting to be a focused, full foray into something revelatory or at least somewhat beautiful," according to Abdurraqib.

  • Generosity While On Tour

    It seems like Drake’s It’s All A Blur tour has made news at every stop since it embarked in early July, and some of the best moments came when the Toronto rapper opened up his wallet to support his dedicated fans. A few of his more impressive giveaways included when he randomly selected an attendee at his Toronto show to receive a six-figure Mercedes-Benz G-Wagon, giving a fan $50,000 after he was allegedly dumped by his girlfriend, and honoring a dedicated fan with an ultimate VIP experience after recognizing them from numerous stops on the tour.

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  • Buying Tupac’s Ring

    Drake purchased Tupac’s crown ring in July for a reported $1.01 million. The Sotheby's auction at which it was presented was held to celebrate the 50th anniversary of Hip-Hop music and culture. The ring was designed by Tupac in 1996, just months before his death. It features a gold circlet studded with a cabochon ruby and two pavé-cut diamonds to form the “crown,” which sits on a diamond-encrusted gold band. It also features the inscription, “Pac & Dada 1996” – a nod to his engagement to Kidada Jones.

  • Release of ‘For All The Dogs’

    Every album Drake releases is an event, and his eighth solo LP, For All The Dogs, was no different. Dropped on October 6, the 6 God gave his fans a wide array of songs with interesting features, which is rather on-brand for him over the past few years. The project also fielded criticism from media pundits like Joe Budden and others for its perceived lack of growth. Regardless, For All The Dogs generated water cooler discussion, which proves that no matter what the Toronto rapper releases, it captures the music world's attention.

  • Friendship With Meek Mill

    Five years after Drake and Meek Mill engaged in their infamous beef, the latter revealed that they are not only cool now with each other but very good friends. Earlier this month, the Philly rapper spoke with Hip Hop Nation and detailed how his relationship with Drizzy has evolved. Among other things, Meek noted that the two texts each other frequently about music and “anything.” “We got that honesty where we can leave it on the table and we can walk away and feel good about that,” he told the program. “And we ain’t had that before the beef.”

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  • Tying Michael Jackson’s Billboard Hot 100 For No. 1 Hits

    Earlier this month, Drake accomplished an impressive feat even for him by tying Michael Jackson’s Billboard Hot 100 record for No. 1 hits. It would ultimately be his For All The Dogs track “First Person Shooter” (featuring J. Cole) that helped him tie up the mark with the king of Pop. Each artist has touted six No. 1 hits to debut at the top spot. Reacting to the news, Drizzy took to his Instagram to post a Photoshopped picture of MJ taking a bathroom mirror selfie while wearing an OVO hoodie. The caption reads, “Mooooooooood @realcoleworld.”

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